Structure

Physi-Chem Properties

Molecular Weight:  396.19
Volume:  426.77
LogP:  6.692
LogD:  3.609
LogS:  -3.603
# Rotatable Bonds:  7
TPSA:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  2.824
Fsp3:  0.292
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.869
MDCK Permeability:  1.4111644304648507e-05
Pgp-inhibitor:  0.73
Pgp-substrate:  0.061
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.887
30% Bioavailability (F30%):  0.243

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  96.3778076171875%
Volume Distribution (VD):  1.469
Pgp-substrate:  4.714828968048096%

ADMET: Metabolism

CYP1A2-inhibitor:  0.635
CYP1A2-substrate:  0.286
CYP2C19-inhibitor:  0.914
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.901
CYP2C9-substrate:  0.916
CYP2D6-inhibitor:  0.596
CYP2D6-substrate:  0.233
CYP3A4-inhibitor:  0.36
CYP3A4-substrate:  0.153

ADMET: Excretion

Clearance (CL):  12.98
Half-life (T1/2):  0.195

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.831
Drug-inuced Liver Injury (DILI):  0.737
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.346
Maximum Recommended Daily Dose:  0.107
Skin Sensitization:  0.852
Carcinogencity:  0.145
Eye Corrosion:  0.003
Eye Irritation:  0.353
Respiratory Toxicity:  0.608

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC98115

Natural Product ID:  NPC98115
Common Name*:   Vismiaphenone D
IUPAC Name:   [2,6-dihydroxy-4-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-(4-hydroxyphenyl)methanone
Synonyms:   Vismiaphenone D
Standard InCHIKey:  FKLXSDINWGPHEI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H28O5/c1-14(2)6-12-18-22(27)20(21(26)16-8-10-17(25)11-9-16)23(28)19(24(18)29-5)13-7-15(3)4/h6-11,25,27-28H,12-13H2,1-5H3
SMILES:  COc1c(CC=C(C)C)c(O)c(c(c1CC=C(C)C)O)C(=O)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463208
PubChem CID:   5675
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000120] Benzophenones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO9701 Vismia cayennensis Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[9917284]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
UNPD: Universal Natural Products Database [PMID: 23638153].
StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
MetaboLights: a metabolomics database [PMID: 27010336].
FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT315 Cell Line CEM-SS Homo sapiens IC50 = 30.0 ug.mL-1 PMID[490699]
NPT1114 Organism Human immunodeficiency virus Human immunodeficiency virus EC50 = 11.0 ug.mL-1 PMID[490699]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC98115 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC186838
1.0 High Similarity NPC274109
1.0 High Similarity NPC12165
1.0 High Similarity NPC477244
1.0 High Similarity NPC168105
1.0 High Similarity NPC25287
1.0 High Similarity NPC477243
1.0 High Similarity NPC1486
1.0 High Similarity NPC41461
1.0 High Similarity NPC66349
1.0 High Similarity NPC477242
1.0 High Similarity NPC249606
1.0 High Similarity NPC150399
0.9924 High Similarity NPC317119
0.9924 High Similarity NPC153979
0.9924 High Similarity NPC472419
0.9923 High Similarity NPC13575
0.9923 High Similarity NPC131039
0.9923 High Similarity NPC156092
0.9848 High Similarity NPC21350
0.9846 High Similarity NPC103842
0.9846 High Similarity NPC286336
0.9774 High Similarity NPC472366
0.9774 High Similarity NPC477956
0.9774 High Similarity NPC470211
0.9769 High Similarity NPC139813
0.9769 High Similarity NPC175098
0.9769 High Similarity NPC27643
0.9769 High Similarity NPC20560
0.9769 High Similarity NPC192304
0.9769 High Similarity NPC56031
0.9769 High Similarity NPC144051
0.9769 High Similarity NPC18877
0.9769 High Similarity NPC472365
0.9769 High Similarity NPC28753
0.9769 High Similarity NPC294593
0.9769 High Similarity NPC159623
0.9769 High Similarity NPC263670
0.9769 High Similarity NPC337373
0.9769 High Similarity NPC312318
0.9769 High Similarity NPC204960
0.9769 High Similarity NPC82225
0.9769 High Similarity NPC242294
0.9769 High Similarity NPC188646
0.9701 High Similarity NPC11056
0.9701 High Similarity NPC80962
0.9701 High Similarity NPC326109
0.9701 High Similarity NPC172250
0.9701 High Similarity NPC213659
0.9701 High Similarity NPC48624
0.9701 High Similarity NPC259166
0.9701 High Similarity NPC144118
0.9701 High Similarity NPC204985
0.9701 High Similarity NPC219917
0.9701 High Similarity NPC215311
0.9699 High Similarity NPC251681
0.9699 High Similarity NPC243528
0.9699 High Similarity NPC471620
0.9692 High Similarity NPC205468
0.9692 High Similarity NPC212631
0.9692 High Similarity NPC129132
0.9692 High Similarity NPC257756
0.9692 High Similarity NPC87231
0.963 High Similarity NPC321980
0.963 High Similarity NPC110969
0.963 High Similarity NPC469404
0.963 High Similarity NPC470089
0.963 High Similarity NPC55832
0.963 High Similarity NPC470087
0.963 High Similarity NPC26051
0.963 High Similarity NPC52789
0.963 High Similarity NPC268204
0.9627 High Similarity NPC295384
0.9627 High Similarity NPC283429
0.9615 High Similarity NPC112192
0.9615 High Similarity NPC189106
0.9615 High Similarity NPC66384
0.9615 High Similarity NPC308037
0.9615 High Similarity NPC186097
0.9615 High Similarity NPC313618
0.9615 High Similarity NPC128348
0.9615 High Similarity NPC164236
0.9615 High Similarity NPC475008
0.9615 High Similarity NPC64359
0.9615 High Similarity NPC309717
0.9615 High Similarity NPC262359
0.9615 High Similarity NPC475009
0.9559 High Similarity NPC226636
0.9559 High Similarity NPC11561
0.9556 High Similarity NPC69769
0.9556 High Similarity NPC253822
0.9556 High Similarity NPC101366
0.9556 High Similarity NPC261227
0.9556 High Similarity NPC241100
0.9556 High Similarity NPC159275
0.9556 High Similarity NPC270883
0.9556 High Similarity NPC172986
0.9552 High Similarity NPC124269
0.9552 High Similarity NPC472368
0.9549 High Similarity NPC472364
0.9549 High Similarity NPC213603
0.9549 High Similarity NPC472367
0.9549 High Similarity NPC473391
0.9549 High Similarity NPC476333
0.9549 High Similarity NPC24394
0.9545 High Similarity NPC164136
0.9542 High Similarity NPC215875
0.9542 High Similarity NPC15834
0.9489 High Similarity NPC475705
0.9489 High Similarity NPC106985
0.9489 High Similarity NPC310130
0.9489 High Similarity NPC245482
0.9489 High Similarity NPC476178
0.9489 High Similarity NPC39329
0.9489 High Similarity NPC143896
0.9489 High Similarity NPC166138
0.9489 High Similarity NPC75049
0.9489 High Similarity NPC175504
0.9489 High Similarity NPC18585
0.9489 High Similarity NPC51887
0.9489 High Similarity NPC221432
0.9489 High Similarity NPC169591
0.9489 High Similarity NPC68104
0.9489 High Similarity NPC164980
0.9489 High Similarity NPC150408
0.9489 High Similarity NPC117836
0.9489 High Similarity NPC301751
0.9489 High Similarity NPC257097
0.9489 High Similarity NPC91560
0.9489 High Similarity NPC149026
0.9485 High Similarity NPC3188
0.9485 High Similarity NPC64908
0.9485 High Similarity NPC147688
0.9485 High Similarity NPC26238
0.9485 High Similarity NPC282300
0.9485 High Similarity NPC118840
0.9485 High Similarity NPC205006
0.9485 High Similarity NPC103362
0.9485 High Similarity NPC156590
0.9481 High Similarity NPC216978
0.9481 High Similarity NPC96565
0.9481 High Similarity NPC303633
0.9481 High Similarity NPC301217
0.9481 High Similarity NPC53181
0.9481 High Similarity NPC217186
0.9481 High Similarity NPC55018
0.9481 High Similarity NPC18260
0.9481 High Similarity NPC220062
0.9481 High Similarity NPC78913
0.9478 High Similarity NPC303644
0.9478 High Similarity NPC209560
0.9478 High Similarity NPC294409
0.9478 High Similarity NPC181124
0.9478 High Similarity NPC162680
0.9478 High Similarity NPC7013
0.9478 High Similarity NPC188879
0.9478 High Similarity NPC23870
0.9478 High Similarity NPC116632
0.947 High Similarity NPC16197
0.9462 High Similarity NPC84772
0.9462 High Similarity NPC247779
0.942 High Similarity NPC234629
0.942 High Similarity NPC311741
0.942 High Similarity NPC473015
0.942 High Similarity NPC197252
0.942 High Similarity NPC328623
0.942 High Similarity NPC209040
0.942 High Similarity NPC473013
0.942 High Similarity NPC236766
0.942 High Similarity NPC476055
0.9416 High Similarity NPC167624
0.9416 High Similarity NPC76338
0.9416 High Similarity NPC220998
0.9416 High Similarity NPC228504
0.9416 High Similarity NPC227579
0.9416 High Similarity NPC78
0.9416 High Similarity NPC10937
0.9416 High Similarity NPC166482
0.9416 High Similarity NPC223500
0.9416 High Similarity NPC328164
0.9416 High Similarity NPC265040
0.9416 High Similarity NPC177354
0.9416 High Similarity NPC64915
0.9416 High Similarity NPC40833
0.9416 High Similarity NPC1089
0.9416 High Similarity NPC125855
0.9416 High Similarity NPC182852
0.9416 High Similarity NPC296917
0.9416 High Similarity NPC144499
0.9416 High Similarity NPC306829
0.9416 High Similarity NPC66515
0.9416 High Similarity NPC76372
0.9416 High Similarity NPC148757
0.9416 High Similarity NPC32739
0.9416 High Similarity NPC324134
0.9416 High Similarity NPC107572
0.9416 High Similarity NPC297600
0.9416 High Similarity NPC148545
0.9416 High Similarity NPC161506
0.9416 High Similarity NPC37496

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC98115 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9615 High Similarity NPD1240 Approved
0.947 High Similarity NPD1607 Approved
0.9328 High Similarity NPD1510 Phase 2
0.9281 High Similarity NPD4378 Clinical (unspecified phase)
0.9143 High Similarity NPD7410 Clinical (unspecified phase)
0.9124 High Similarity NPD1549 Phase 2
0.9051 High Similarity NPD1552 Clinical (unspecified phase)
0.9051 High Similarity NPD1550 Clinical (unspecified phase)
0.8958 High Similarity NPD4380 Phase 2
0.8897 High Similarity NPD7411 Suspended
0.8841 High Similarity NPD2796 Approved
0.8776 High Similarity NPD2393 Clinical (unspecified phase)
0.8759 High Similarity NPD6651 Approved
0.8725 High Similarity NPD7075 Discontinued
0.8716 High Similarity NPD8443 Clinical (unspecified phase)
0.8705 High Similarity NPD2935 Discontinued
0.8671 High Similarity NPD6799 Approved
0.8649 High Similarity NPD7096 Clinical (unspecified phase)
0.8649 High Similarity NPD7819 Suspended
0.8581 High Similarity NPD6801 Discontinued
0.8521 High Similarity NPD7421 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD1934 Approved
0.8451 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8446 Intermediate Similarity NPD6599 Discontinued
0.8414 Intermediate Similarity NPD1511 Approved
0.8411 Intermediate Similarity NPD7768 Phase 2
0.8411 Intermediate Similarity NPD3882 Suspended
0.84 Intermediate Similarity NPD2801 Approved
0.8392 Intermediate Similarity NPD2800 Approved
0.8387 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD3750 Approved
0.8333 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.831 Intermediate Similarity NPD1551 Phase 2
0.8299 Intermediate Similarity NPD1512 Approved
0.8264 Intermediate Similarity NPD1243 Approved
0.8258 Intermediate Similarity NPD6232 Discontinued
0.8239 Intermediate Similarity NPD2799 Discontinued
0.8239 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8231 Intermediate Similarity NPD2533 Approved
0.8231 Intermediate Similarity NPD2532 Approved
0.8231 Intermediate Similarity NPD2534 Approved
0.8217 Intermediate Similarity NPD7473 Discontinued
0.8214 Intermediate Similarity NPD943 Approved
0.8194 Intermediate Similarity NPD6959 Discontinued
0.8125 Intermediate Similarity NPD5953 Discontinued
0.8125 Intermediate Similarity NPD2344 Approved
0.8121 Intermediate Similarity NPD920 Approved
0.8117 Intermediate Similarity NPD3749 Approved
0.8113 Intermediate Similarity NPD7286 Phase 2
0.8113 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8102 Intermediate Similarity NPD1203 Approved
0.8095 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD2798 Approved
0.8038 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD6166 Phase 2
0.8038 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD3972 Approved
0.8014 Intermediate Similarity NPD2654 Approved
0.8013 Intermediate Similarity NPD5494 Approved
0.8 Intermediate Similarity NPD5403 Approved
0.7987 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD3817 Phase 2
0.7986 Intermediate Similarity NPD3748 Approved
0.7943 Intermediate Similarity NPD2313 Discontinued
0.7937 Intermediate Similarity NPD3818 Discontinued
0.7929 Intermediate Similarity NPD6832 Phase 2
0.7919 Intermediate Similarity NPD7390 Discontinued
0.7914 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD2309 Approved
0.7895 Intermediate Similarity NPD9493 Approved
0.7883 Intermediate Similarity NPD9717 Approved
0.7867 Intermediate Similarity NPD5401 Approved
0.7853 Intermediate Similarity NPD6559 Discontinued
0.784 Intermediate Similarity NPD7074 Phase 3
0.7838 Intermediate Similarity NPD4628 Phase 3
0.7821 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7054 Approved
0.7778 Intermediate Similarity NPD9545 Approved
0.7778 Intermediate Similarity NPD3226 Approved
0.7763 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD7472 Approved
0.7722 Intermediate Similarity NPD919 Approved
0.7714 Intermediate Similarity NPD1164 Approved
0.7692 Intermediate Similarity NPD3268 Approved
0.7687 Intermediate Similarity NPD6100 Approved
0.7687 Intermediate Similarity NPD6099 Approved
0.7683 Intermediate Similarity NPD6797 Phase 2
0.7681 Intermediate Similarity NPD422 Phase 1
0.7676 Intermediate Similarity NPD4908 Phase 1
0.7669 Intermediate Similarity NPD5844 Phase 1
0.7662 Intermediate Similarity NPD7458 Discontinued
0.7647 Intermediate Similarity NPD1548 Phase 1
0.7643 Intermediate Similarity NPD5402 Approved
0.764 Intermediate Similarity NPD3926 Phase 2
0.7636 Intermediate Similarity NPD7251 Discontinued
0.7635 Intermediate Similarity NPD2346 Discontinued
0.7625 Intermediate Similarity NPD1247 Approved
0.7622 Intermediate Similarity NPD1729 Discontinued
0.7619 Intermediate Similarity NPD7033 Discontinued
0.76 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7003 Approved
0.7591 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7808 Phase 3
0.7589 Intermediate Similarity NPD1470 Approved
0.7589 Intermediate Similarity NPD2797 Approved
0.7578 Intermediate Similarity NPD5710 Approved
0.7578 Intermediate Similarity NPD5711 Approved
0.7568 Intermediate Similarity NPD5404 Approved
0.7568 Intermediate Similarity NPD5405 Approved
0.7568 Intermediate Similarity NPD5408 Approved
0.7568 Intermediate Similarity NPD5406 Approved
0.7554 Intermediate Similarity NPD1610 Phase 2
0.7554 Intermediate Similarity NPD1201 Approved
0.7534 Intermediate Similarity NPD230 Phase 1
0.7518 Intermediate Similarity NPD1876 Approved
0.75 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4308 Phase 3
0.7485 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD4360 Phase 2
0.7457 Intermediate Similarity NPD4363 Phase 3
0.7452 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD3764 Approved
0.7415 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD1933 Approved
0.7415 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD5124 Phase 1
0.7414 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD4361 Phase 2
0.7407 Intermediate Similarity NPD1241 Discontinued
0.7394 Intermediate Similarity NPD3225 Approved
0.7379 Intermediate Similarity NPD3027 Phase 3
0.7379 Intermediate Similarity NPD4625 Phase 3
0.7376 Intermediate Similarity NPD1608 Approved
0.7365 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD1465 Phase 2
0.7343 Intermediate Similarity NPD3267 Approved
0.7343 Intermediate Similarity NPD3266 Approved
0.7341 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1651 Approved
0.7338 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD411 Approved
0.7329 Intermediate Similarity NPD1296 Phase 2
0.7324 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD6104 Discontinued
0.7312 Intermediate Similarity NPD2296 Approved
0.7312 Intermediate Similarity NPD4288 Approved
0.7297 Intermediate Similarity NPD447 Suspended
0.7293 Intermediate Similarity NPD9266 Approved
0.7293 Intermediate Similarity NPD74 Approved
0.7292 Intermediate Similarity NPD1019 Discontinued
0.7285 Intermediate Similarity NPD1471 Phase 3
0.7285 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1283 Approved
0.7247 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5049 Phase 3
0.7241 Intermediate Similarity NPD9494 Approved
0.7234 Intermediate Similarity NPD3847 Discontinued
0.7233 Intermediate Similarity NPD5890 Approved
0.7233 Intermediate Similarity NPD5889 Approved
0.7231 Intermediate Similarity NPD940 Approved
0.7231 Intermediate Similarity NPD846 Approved
0.723 Intermediate Similarity NPD4307 Phase 2
0.7218 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD9263 Approved
0.7218 Intermediate Similarity NPD9267 Approved
0.7218 Intermediate Similarity NPD9264 Approved
0.7215 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD6798 Discontinued
0.7208 Intermediate Similarity NPD2354 Approved
0.7203 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4662 Approved
0.7179 Intermediate Similarity NPD4661 Approved
0.717 Intermediate Similarity NPD6585 Discontinued
0.7163 Intermediate Similarity NPD4626 Approved
0.7163 Intermediate Similarity NPD17 Approved
0.7152 Intermediate Similarity NPD7229 Phase 3
0.7133 Intermediate Similarity NPD1481 Phase 2
0.7126 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4287 Approved
0.7123 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1613 Approved
0.7114 Intermediate Similarity NPD3142 Approved
0.7114 Intermediate Similarity NPD3140 Approved
0.7105 Intermediate Similarity NPD4477 Approved
0.7105 Intermediate Similarity NPD4476 Approved
0.7104 Intermediate Similarity NPD7584 Approved
0.7097 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3887 Approved
0.7083 Intermediate Similarity NPD4749 Approved
0.7081 Intermediate Similarity NPD6280 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data